


The Greatest Night of Dipper's Life

by AnimationFemdomination



Category: Gravity Falls
Genre: Crop Top, Dominatrix, F/F, F/M, Femdom, Teasing
Language: English
Status: Completed
Published: 2018-01-25
Updated: 2018-01-25
Packaged: 2019-03-09 06:57:16
Rating: Mature
Warnings: Rape/Non-Con, Underage
Chapters: 5
Words: 3,480
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13476120
Author URL: https://archiveofourown.org/users/AnimationFemdomination/pseuds/AnimationFemdomination
Summary: Wendy wears an outfit that pushes Dipper over the edge.





	1. Windy Wendy

**Author's Note:**

> My most ambitious work yet. Multiple chapters and humor thrown in for good measure. Main NSFW content is in chapter 4.
> 
> Image edit by me.

**Summary for the Chapter:**

> Windy's outfit gets a lot of air to her body.

Having grown up as a city boy, Dipper found the many quirks of small-town life in Gravity Falls, Oregon to be completely new experiences. Whether it was celebrating Halloween during the summer or throwing birdseed at the mayor elect, the town never ceased to surprise him. Yet it was rural women’s fashion which shocked the boy most.

On the day of the annual Woodstick Festival, Dipper looked forward to having a normal, enjoyable time at the concert with his newfound friend group. Such thoughts were quickly dispelled, however, when he entered Thompson’s garage.

Casually standing there was Wendy Corduroy, the girl whom Dipper had fantasized over. Foregoing her usual green flannel and jeans, Wendy donned an outfit unlike anything the young boy had ever seen. Her Daisy Dukes framed the teenager’s long, pale legs nicely. Though they were stunning, Dipper had gotten a good look at them during his short-lived job as a pool boy thanks to her one-piece bikini. It was Wendy’s choice of top, however, which captivated the hormone-filled boy.

For the concert, the tomboy had decided on a light blue, sleeveless crop top with frills. It was simple enough, and combined with the colorful headband which accentuated her voluptuous red hair, Wendy’s look as a hippie goddess was complete. Yet crop tops were a completely foreign concept to Dipper. Upon first sight of it, he awkwardly stared at her torso for an uncomfortable amount of time. Thankfully, she hadn’t seemed to notice and he quickly stopped staring at her, but he continued to sneak peeks throughout the evening.

“What is that?” thought Dipper. “It’s definitely not a bikini. It’s like a shirt, but… I get to see her belly?”

Dipper was profoundly mesmerized. In addition to showing off the full extent of her arms, Wendy’s stomach was visible for the first time to him. She was rather thin but showed definite signs of ab muscles. Dipper looked to the other guys to see if they were taken aback at all. Though they seemed as casual as ever, the perceptive young boy could tell they were aware of their friend’s scandalous attire.

“Is that legal?” wondered Dipper. “Well laws in Gravity Falls are weird anyway. But why would she wear something like that unless she was trying to show off? With those shorts, it’s like she’s naked.”

The boy blushed as he continued to admire the girl of his dreams before wiping away a bit of drool. Taking a closer look at the beautiful girl before him, Dipper watched how her belly contracted and expanded as she spoke and breathed. Her belly button cutely curved inward, and Dipper wanted nothing more than to rub his hands along her toned sides. She seemed very confident in her pale skin, and he wondered if she cut the hem on the shirt herself.

Dipper’s predicament worsened, however, as he felt a stiff poking at the front of his jeans. He knew there was no way out of this situation. He daydreamed about Wendy putting on her shorts and shirt, looking in the mirror, and thinking it’s ok to wear in public. Before long, a strange feeling washed over the boy. He shifted uneasily while standing as his eyes rolled back. Dipper’s shoulders slumped as he felt an incredible experience nearly bring him to his knees. When it was over, he walked over to a workbench and rested his elbows on the table.

“Oh my gosh… Did I just-“ Dipper peered down at his lower half. Though not visible, he could feel a sizable amount of liquid staining his underwear.

“What?! While standing up?! And not even touching it?!” he thought. “That’s possible?! You can do that?!” Dipper was utterly stunned. He felt even more infatuated with Wendy. She was indeed like a goddess, and he but the mere mortal who cowers and trembles before the gift of her beautiful sight.

Mabel soon arrived and fueled relationship drama, splitting the group apart. Dipper knew he would have to help make things right if he wanted to continue to hang out with his cool, older friends and help Mabel cheer up. Though his thoughts lingered, Dipper focused on helping Mabel make amends. As they left the garage, Dipper was reminded of his sister’s innocence.

“Come on, bro-bro, we gotta-… Wait, um, what’s that smell?” asked the sweet girl.

“Uh, uh, it’s nothing!” he hastily replied.

“What do you mean it’s nothing? I definitely smell something! Come on, what did you eat?” Mabel attempted to pry open Dipper’s mouth, but he quickly pushed her back.

“Ok, you caught me! It was, um, the Lumberjack Special from Greasy’s Diner! Yep, yep, that’s it. Sorry I didn’t save you any” said Dipper.

“Oh, well why didn’t you say so? It smells so good, I just wanna put it in my mouth right now!” said Mabel as she imagined what it tastes like.

Embarrassed, Dipper walked out with his sister as he considered the implications of her statement.

**Notes for the Chapter:**

> Please leave a comment. I also take requests.


	2. Mabel's Birds and Bees

**Summary for the Chapter:**

> Mabel knows more than Dipper thinks.

Later that night, Dipper lied awake in bed as his thoughts drifted back to Wendy. As the twins were not yet asleep and still had the lights on, Mabel spoke up.

“So how’d you like the festival?” asked Mabel as she turned on her bed lying towards Dipper, hand resting on her head.

“Huh? Oh, it was ok, I guess” replied Dipper.

“Yeah. Grunkle Stan’s ‘I EAT KIDS’ balloon had to be the highlight of the day.”

Dipper chuckled. “Yeah, maybe even the whole summer. Those kids will be scarred for life.”

“Wendy looked pretty hot too.”

Taken completely off guard, Dipper nearly fell out of his bed. “Wh- I mean, yeah, sure, I guess… Did that really just come out of your mouth?”

This time, Mabel chuckled. “You know it, bro-bro.”

Dipper’s cheeks reddened as he considered their conversation at the garage earlier. His fears came true when Mabel spoke up.

“So the Lumberjack Special at Greasy’s Diner, huh?” asked Mabel coyly.

Dipper felt light-headed. “Uh, um, yeah…” he stuttered.

Mabel flashed a great smile. “They might want to change the recipe, because it smells like cum to me.”

Horrified, Dipper laughed awkwardly at his sister’s remark. “Well, guess we better get off to sleep. Big day ahead of us tomorrow. Good night, sis.”

Before he could turn off the lights, Mabel pushed his hand from the lamp switch.

“Did the Little Dipper turn into the Big Dipper today?” asked Mabel cheekily.

Dipper knew there was no way out of this. With his sister, even the slightest embarrassment was fair game for her tongue-and-cheek jokes.

The boy sighed. “How do you know this stuff?”

“Remember that body-switching carpet?” questioned the young girl.

“Yeah…”

“Well Grunkle Stan read me some, uh, very mature literature.”

“So that’s why he thinks I know these things!” said Dipper. “But that still doesn’t explain everything.”

“Well, ever since that miniature golf match, Pacifica and I have become close friends. Really close friends.”

“Oh, I see. Well I’m glad your happy and free to be yourself!” said Dipper.

“Like, if I was a baseball player, I’d be on the away team” said Mabel.

“Gotcha.”

“I play for the other team.”

“Yeah, I got it.”

“I’m a lesbian, Dipper.”

“I know!” he exclaimed.

“So just how did you get away with that earlier?” asked Mabel. “You know, considering you had a lot of ‘cumpany’.” Mabel slapped her knee and laughed at her own joke. Dipper was not amused.

“Well, luckily I didn’t stand too close to anyone else afterwards. Apparently they would’ve smelled it. And, well, I actually didn’t touch it…” he said.

“What?!” screamed Mabel. Dipper motioned for his sister to keep her voice down. Mabel screamed in her pillow. “Oh my gosh, bro-bro, I didn’t know that was possible!”

“Yeah, me neither…” replied Dipper.

“Wendy in a crop top will really do that to you?”

“Crop top? That’s what that shirt’s called?” questioned Dipper.

“Oh yeah. Anybody can wear them. Robbie’s got some. But I think Wendy looks better. You know, because I’m-“

“A lesbian, yeah” interrupted Dipper.

Mabel hopped out of her bed. “I made my own one. You wanna see?”

“No, no thanks, I’m all right” stated Dipper. Wendy was enough for the hormone-filled kid, he didn’t want to start thinking of his own sister that way as well.

Mabel sat back on her bed. “Suit yourself.”

“Why does she wear it? Is it to show off?” asked Dipper.

“Girls can wear whatever they want, Dipper. It doesn’t have anything to do with how promiscuous they are… Promiscuous… Pro-mis-cuous… What a weird word. That was in the book Grunkle Stan read to me. Or you, I guess” sidetracked Mabel.

“Of course, sorry for thinking that” said Dipper.

Mabel smiled. “That said, Wendy definitely wants the D… I-P-P-E-R”

He didn’t want to, but Dipper couldn’t help but smirk at his sister’s silly nature. Even on the most serious of subjects, she managed to still be Mabel.

“So where do I go from here?” asked the boy.

“Well, I say we push this to the limit. When was the last time you masturbated?”

Dipper didn’t enjoy hearing his sister say that word, but still felt comfortable talking with her about the mature topic. “… Yesterday, so?”

“So?! Wasn’t today’s the best you’ve ever felt?”

“Yeah, I mean, if it counts…” replied Dipper.

“So imagine what it’d be like if you went a week without masturbating?”

Dipper considered the challenge and concluded that the outcome would indeed be unimaginable euphoria.

“That’s a good idea. Yeah, ok. I’ll do that” said Dipper.

“Good. And hey, if I hear any suspicious rustling over in your bed, I’m bringing out my crop top” said Mabel.

Mabel turned off the light, and the twins went to bed.

**Notes for the Chapter:**

> Please leave a comment. I also take requests.


	3. A Long Week

**Summary for the Chapter:**

> Dipper manages to get through the week.

Dipper’s week-long challenge proved difficult for the boy. Wendy invited him to join her and her friends at the pool, but he politely turned down the offer. He knew it would spell disaster. By the grace of the Love God, Dipper made it to the end of the week without masturbating.

In their bedroom, Mabel giddily bounced up and down on her bed.

“You made it a full week, I’m so proud of you!” The girl took out an oddly specific sticker of a surfer dude at the beach giving a thumbs up with the caption, “I went one week without masturbating!” and placed it on Dipper’s shirt.

“Where do you even find these stickers?” he asked.

“I have my ways” replied Mabel mysteriously.

“Hey, I never asked, did you take the challenge yourself?”

“Well, technically, yes, I didn’t masturbate for one week. But Pacifica and I-“

“Ok, I got it.”

“No really Dipper, you’re gonna wanna hear this. So Pacifica has this leather-“

“Mabel, please! I’ve made it this far, I can’t think about Pacifica” he said.

“Understandable” said Mabel.

“So what happens now?” asked Dipper.

“Now the fun begins. But first, you have to go to sleep. Trust me, you can thank me later.”

“Wh-” Before Dipper could react, his sister placed a pillow over his face.

**Notes for the Chapter:**

> Please leave a comment. I also take requests.


	4. City Folk Just Don't Get It

**Summary for the Chapter:**

> Dipper discovers the perks of Wendy.

The next thing he knew, Dipper woke up naked in an empty room with his wrists and ankles tied to a table. Wendy then walked in, and Dipper’s mouth dropped. She wore her boots and Daisy Duke jean shorts like before, but also had on a modified version of her typical green flannel shirt. The sleeves cut off, its hem was much shorter than before and tied up in a bow just below her breasts. She was a model country girl.

Wendy swished her long, flowing red hair. “Hey Dipper.”

“W-Wendy? How did you-”

“Mabel told me all about your little situation” she interrupted. “I’m happy to oblige.”

“You… You are?” bemused Dipper.

Wendy bent down to the young boy’s ear. “Yes…” she whispered. “I want to make this a night you’ll never forget. Years from now, you’ll have moved on from Gravity Falls and meet other girls, but none of them will be as good as me. Oh sure, they can give you handjobs, they can give you blowjobs, they can even fuck you, but they can never give you what I can.”

“Wh-… What’s that?” asked the lucky boy.

Wendy smiled. “The greatest experience of your life.”

Dipper drooled with anticipation.

“After this, it’s all downhill from here, dude. You’ll come across other sluts, but they won’t be good enough. You’ll pretend it’s my soft hands around your dick, my sweet mouth sucking your cock, or my pussy enveloping you. But it won’t be. You’ll fantasize about me, but it won’t feel as good, and you’ll be sad you can’t go back and relive today.”

Wendy’s sexual ASMR was enough to drive Dipper wild. Struggling with his hands, he remembered he was tied to the table. Looking down at his member, he noticed it was more erect than it had ever been. Its immense girth and length was very impressive for his age, but something was wrong. He noticed a strange cock ring stifling him from ejaculation.

“Oh, that little thing? You can’t find it in your local toyshop. That cock ring is specially designed to stop you from cumming. It isn’t too tight and allows you to feel all the buildup happening, but presses on a very specific point to stop you from climaxing.”

“That’s the worst… And best thing I’ve ever heard” mustered Dipper. “Where did you even find it?”

Wendy smiled. “Mabel found it.”

“Mabel?!” said Dipper shocked. “But how did she- Pacifica, she has access to everything!”

“And I have access to you…” said Wendy as she traced her finger in and around Dipper’s belly button. He could sense her perfectly-manicured nails.

Dipper gulped. “So what do you wanna do first? I, uhhhh-”

Dipper lost his train of thought as Wendy began teasing his nipples.

“I saw you shirtless at the pool” she said. “It’s not fair that girls can’t be shirtless too. Have you ever seen a woman’s breasts before?”

“N-no ma’am…” muttered Dipper. Wendy didn’t even command him to call her ma’am, but she liked it. Smiling, she pulled her tits out of her tight shirt. Bouncing back into place, she cupped them and began to lick her nipples and large aureolas.

“What do you think?” she asked.

“They’re amazing” said the boy with wide, mesmerized eyes.

“Really? Because they’re not as big as some other girls, and they’re pale like me too” said Wendy as she cutely stomped her foot and put up a pouty face.

“No, they’re perfect” said Dipper as if in a trance. “They are unmatched by any girl in the world.”

“You should know, I hear you’ve got a scandalous Internet history” said Wendy coyly. “But nothing compares to the real thing.”

Dipper nodded, continued to be in his trance. Like a hypnotist, Wendy shook them back and forth, and Dipper’s eyes swayed.

“You wanna touch them? Feel them? Lick them?”

Dipper nodded excitedly. Wendy lowered her breasts right above Dipper. Upset, he tried lifting his head and sticking out his tongue out, but they were just shy of reach.

“What’s wrong, Dipper? Don’t you like them? They’re right here” she teased.

“Wendy, please” begged Dipper.

“You pathetic little boy. Here, let Wendy help you.” She planted her pale tits on his chest, rubbing them around as her nipples teased his nipples. Dipper’s member wanted to explode but just couldn’t.

Wendy lifted them back up. “Maybe you like boobs, or maybe you're an ass man?” She began to twerk in front of his face.

“I, um, I like them all” said Dipper awkwardly. Wendy laughed.

Wendy began to slip off her jean shorts, only revealing her backside towards Dipper.

“Well?” she asked expectedly.

“Perfect…” he said.

Wendy continued to twerk in front of Dipper’s face. He tried to reach out and touch her asscheeks but couldn’t move his hands enough.

“Are you really looking at my ass? Or maybe you’re a leg man? Not as common, but just as fun.” Lifting her shorts back up, Wendy displayed her thighs for Dipper, rubbing her legs, stretching them, and showing them off from different angles.

“I…” is all Dipper could say.

“Like them all, good” finished Wendy. “You like these shorts? I picked them just for you, Dipper.”

“Yes…” he said.

“They’re not too short?” she asked.

“No way…” he replied.

“Actually, they are” she corrected. “That’s why I like them.”

Dipper’s dick was begging for attention. He felt like he could explode at any moment but was unable to.

“Now let’s get down to business. The real stuff” said Wendy. “I’m not wearing any panties, Dipper. See?”

Wendy positioned herself so that Dipper could see up her shorts. He could almost see her private area.

“If you’ve never seen tits before, I know you’ve never seen a vagina in person. Think you’re ready?” questioned Wendy.

Though tied to the table, Dipper flexed his muscles as if to prove his manliness. “I’m ready.”

Wendy smiled and took off her Daisy Dukes, this time turning her front towards the boy. Dipper’s mind went wild as Wendy played with herself, the mushy sound of her rhythmic circling driving the boy nuts. Soon, Dipper felt like a water hose with a rock blocking the nozzle. He was going to let it out.

“Oh my gosh, Wendy, I think… I think I’m gonna…” he said panting.

“No way, dude. That thing’s unbeatable.”

“No seriously, Wendy. Oh my gosh. I’m gonna cum. What do I do? What’s gonna happen?”

Wendy began to worry and pulled her jean shorts back up. “Just don’t think of me, ok?”

“But, oh my gosh, but Wendy! Your outfit is hot!”

“Damn dude, you’re right.”

“What? That’s not helping!”

With Wendy’s body hunching over him, it was if Dipper was seeing her for the first time again. The way she just stood there, her pale midriff, arms, and legs completely exposed. The smell of her exposed skin and vagina still lingering. Her eyes looking directly into him, a worried and caring expression on her face.

Finally, it was like the rock was lifted. Dipper began to orgasm, only no semen was coming out of him. After a very short while, Wendy began to worry further.

“You’re still going?” she asked incredulously. Dipper was rendered unable to respond. A minute passed and he still felt the full extent of orgasmic euphoria.

“Jeez dude, this isn’t supposed to happen! You’re not supposed to be able to cum with this thing!” Dipper still couldn’t say anything, only grovel and twist while tied to the table.

“I heard male pigs orgasm for half an hour. Guess you’re gonna see what it’s like to be Waddles?” bemused Wendy hopefully.

Thirty minutes passed, and Dipper felt the full extent of every moment of it. When it was finally over, he collapsed.

**Notes for the Chapter:**

> Please leave a comment. I also take requests.


	5. Time Twins

**Summary for the Chapter:**

> Time travel logic is weird.

**Notes for the Chapter:**

> Just a silly goof.

Dipper woke back up in a hospital bed.

“Wh-… Where am I?” he asked.

“You’re in a hospital.” Dipper turned and saw Mabel by his bedside.

“What happened?” asked Dipper.

“Well, let’s just say Wendy was true to her word” said Mabel.

“Oh, right. I remember now” said Dipper. “She’s right though. I will never be in such a blissful state as that day.”

“Don’t be so sure” said Mabel. Reaching into her skirt, Mabel pulled out Blendin Blandin’s time tape and handed it to Dipper.

“Where did you?…”

“What, haven’t you ever played tennis? We don’t have pockets! Lots of girls store stuff this way.”

“No, I mean-“ Dipper sniffed the time tape. Yep, it smelled like Mabel. “No, I mean where did you even get this?”

“I have my ways” winked Mabel. “So are you gonna use it?”

“I don’t know… I feel like there’s way better uses of a time machine.”

“Do you really? I mean, with all that jibber jabber about butterflies and blue people?” asked Mabel. “If you’re not gonna use it, I will. I’d like to go back to last night with Pacifica.” Dipper pulled the time tape towards his chest. There was a flash.

“No, actually, I’d like to use the time tape” he said. “But you can use it after me.”

“What are you talking about?” asked Mabel. “I just used it.”

“Huh?” wondered Dipper.

“Oh, is this the timeline where you use it first? Sorry, I’m off by like 30 seconds. I missed the beginning of our conversation” said Mabel.

“How… How many times have you used this?” questioned Dipper.

“You mean how many times have we used this?” There was another flash.

“No, in this timeline, I haven’t used it.”

“Used what? I just got here. Oh, the time tape?”

“You know what, no.” Dipper smashed the time tape and there was another flash. “Sorry Mabel, but destroying it was the best thing to do.”

“Aw, but I never got to use it!” said Mabel. Dipper sighed.

**Notes for the Chapter:**

> Thanks for reading everything. Hope you enjoyed it.

**Author's Note:**

> Please leave a comment. I also take requests.


End file.
